Acetic Acid → HCID 57635075, compound

To a solution of 2.1 g (0.014 mole) of 2-methyl-3-oxo-butanoic acid ethyl ester and 40 mL of dichloroethane was added 1.37 g (0.016 mole) of cyclopentylamine. The mixture was stirred for 1.5 hours, then 4.63 g (0.020 mole) of sodium triacetoxyborohydride and 0.84 g (0.014 mole) of acetic acid were added. The mixture was stirred at room temperature for 24 hours and then quenched by the addition of 50 mL of saturated aqueous sodium bicarbonate. After 20 minutes, the organic layer was separated and the aqueous layer was extracted twice with 30 mL of dichloromethane. The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated to afford the crude product as yellow oil. Purification of the residue by silica gel chromatography, eluting with hexanes-ethyl acetate (30:70) gave 1.5 g of (rac)-3-cyclopentylamino-2-methyl-butanoic acid ethyl ester.

1. stirringThe mixture was stirred at room temperature for 24 hours
2. customquenched by the addition of 50 mL of saturated aqueous sodium bicarbonate
3. waitAfter 20 minutes
4. customthe organic layer was separated
5. extractionthe aqueous layer was extracted twice with 30 mL of dichloromethane
6. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customto afford the crude product as yellow oil
10. customPurification of the residue by silica gel chromatography
11. washeluting with hexanes-ethyl acetate (30:70)

ORD record

ord-6067cbd46aff46e7aefcbf9516c4e287

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07517873B2